Roger Jones Wins ASD Handicapping Challenge for Third Time

Sep 18, 2025 | Handicapping, Live Racing, The Inside Track

Roger Jones with his ASD Handicapping Challenge trophy at the Fan Education booth. Fellow handicapper and fan educator Brad Ostrove on the right. Stop by and ask them a question when you’re at the track. Smart guys! (George Williams Photo)

By G.S. Thompson

Roger Jones won the ASD Handicapping Challenge for the third time last Tuesday, and he’s going to Vegas with his girlfriend and fellow contest winner Nicole Baker at the end of October to celebrate with his $3,500 prize money.

It was the fourth overall tournament win at Assiniboia Downs for the 54-year-old bus operator, but his first win in the live contest in about eight years. It also vaulted Jones to the top of the standings in the Handicapper of the Year contest.

Jones built his bankroll to $77.60 with a combination of medium-priced horses and favorites to best runner-up Steve Holborn ($70.80) by $6.80, followed by Wayne Misko ($64.10) and Bonnie Simmons, who finished in a dead heat for third place.

Race-by-Race Picks

Jones’s path to victory began conservatively. “The first two races, I took the favourites,” he said. Both horses delivered, giving him a solid foundation. But in the third race, his strategy began separating him from the field.

Instead of playing favourite Mechanic Susie, Jones went with 15-1 Dazzling Gold, who delivered a crucial second-place finish that paid more than the winner across the board. The fourth race proved challenging, with Jones struggling to find value among uninspiring favourites. He settled on Dreamin Out Loud, who finished second, but in races five and six Jones distanced himself from the competition.

In the fifth race, Jones demonstrated his ability to adapt based on track conditions. “I actually went with the horse that I didn’t originally have because I thought the track was playing a bit for  speed,” said Jones. His selection, It’s a Fluke, trained by Monique Goulet after being claimed and fitted with blinkers, won at 4-1.

It’s a Fluke wins the fifth race last Tuesday for trainer Monique Goulet. Antonio Whitehall up. (Jason Halstead / Assiniboia Photo)

The sixth race featured what Jones considered a standout opportunity. “From a contest standpoint, I think that around 75% of the people should have had the horse in the next race,” said Jones, referring to Enano Caro. “That horse looked like it was going to get the lead and it was paying 9-1. To me, you had to take this horse.”

Enano Caro’s odds dropped to 7/2, but he came through with a solid win, and only 13 others in the contest had him. Entering the final race, Jones faced a strategic dilemma. While he identified a 25-1 longshot as having a good chance to win, he opted for the logical favorite Go Fer, who survived a determined challenge from the 56-1 longshot Jones liked, Pino Bambino, to secure the tournament win.

Handicapping Philosophy and Angles

Jones’ success stems from decades of study. Having played horses for nearly 40 years, he’s developed a sophisticated approach incorporating multiple angles. “I learned a lot from Ivan Bigg and Marshall Posner,” said Jones. “I like to listen to what people say and see if it’s something that fits for me.”

One of Jones’ favourite angles involves horses that have run well in their previous races, despite adverse circumstances “I like it when they show something when things didn’t go their way,” said Jones, who particularly values fourth-place finishes, noting that “people just seem to discount a horse” when they finish fourth in their previous races.

Jones also incorporates breeding analysis using pedigreequery.com and pays close attention to equipment changes like blinkers, though context matters. “Blinkers in itself isn’t a positive angle,” said Jones, “But if you can find a reason why the blinkers are going on, that makes a difference.” An expert quarter horse handicapper, another angle Jones carried over from those runners to thoroughbreds is class. “It works with both quarter horses and thoroughbreds,” said Jones.

The Value of ASD Contests

September ASD Handicapping Challenge winners. L to R: runner-up Steve Holborn, Simulcast & Program Director Sheri Glendinning, winner Roger Jones, third-place finishers Wayne Misko and Bonnie Simmonds. (Jason Halstead /Assiniboia Photo)

Jones is a strong advocate for Assiniboia Downs’ handicapping contests, citing their positive expected value (EV). “I love the contests,” he said. “It’s one of the best things they have going on at the Downs here. The EV is high. I don’t know why everybody doesn’t play in them.”

When not competing or driving people around the city, Jones works at the Fan Education Booth, on the main floor of the grandstand, helping newcomers understand handicapping basics. “A lot of people are brand new,” said Jones. “But you can learn from anybody, and something new from every race you play.”

Jones is looking forward to his Vegas trip with his girlfriend, which coincides with the Breeders’ Cup on October 31 and November 1 at Del Mar.

He’ll have all the class he needs there.